


To Sleep Perchance To Dream

by nugget_basket



Category: Supernatural
Genre: Depression, Goddammit, M/M, Oh god, Suicide, i'M SAD, it's sad
Language: English
Status: In-Progress
Published: 2013-11-07
Updated: 2013-12-14
Packaged: 2017-12-31 18:32:12
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 17,649
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1035003
Author URL: https://archiveofourown.org/users/nugget_basket/pseuds/nugget_basket
Summary: <blockquote class="userstuff">
              <p>Dean Winchester has had a shitty life. His parents died in a fire when he and his brother Sam were little, and since then, it hasn't been easy. Bobby was the only lighthouse in the churning sea that was his life, and now the light's out.</p><p>There's only one thing left to do.</p><p>(This is a darker fic. While I am known to write a LOT of fluff, this isn't one of them.)<br/>MY APOLOGIES. This will kept WIP for personal reasons.</p>
            </blockquote>





	1. Down the Drain

**Author's Note:**

> When I wrote this I hoped that somehow people would be able to relate to it. Yeah, Dean goes through a lot, but we’ve all had our fair share of crap, and our problems aren’t any less or more than anyone else’s. The poem Dean quotes is ‘No’ by A.M Juster. I will not be continuing this fic that soon, but please inform me if you would like it to be continued. I wasn’t sure if it would be well received. If I should continue, most likely the updates will be weekly. Do comment and tell me what you think! I have had trouble continuing it, since it's not my usual style. (Do let me know if it's something you want me to update, and turn into a weekly fic.)
> 
> There have been some plot changes, and the editing is a little wonky. My apologies! Sam's step dad is Gabriel not Balthazar! So sorry :/

“I’m sorry about Bobby, kid.” Rufus’ gruff voice echoed within Dean’s ears and it took him a moment to realize he was being spoken to, and then another moment to decipher what the fuck Rufus was talking about.

“Yeah. Me too.” Dean replied.

 Bobby didn’t want a proper funeral or anything, so his close friends all showed up to watch as his coffin was lowered six feet into the cold, damp earth. It started raining as the guys were filling up the grave, digging their shovels into piles of brown sandy mush, and dumping it onto the black casket. As droplets of water landed on exposed parts of the casket, turning into a matt sort of colour, Dean’s head entered a stage of surprising clarity. Rufus squeezed his shoulder before walking away. The small crowd filled with Bobby’s friends and customers, all people whose lives Bobby had somehow touched, began to dissipate like smoke. Chattering softly, some offered their condolences to Dean as they walked away. The tell tale sound of umbrellas being opened made Dean look up, half expecting to see black umbrellas open around him, like some movie scene. Dean almost laughed when umbrellas of shades like red, indigo and white opened up around him, as people hurried back to their cars, parked along the road outside the cemetery.

The rain was getting heavier, progressing from a thin mist into an actual downpour. Dean’s leather jacket, the only possession he had left from his father was soaked, and a small part worried that it would be ruined if he didn’t get out of the rain and let it dry. Dean just stood there, looking at nothing in particular. The cemetery didn’t have the stink of death or the fog of despair that it should have had, considering it’s where people were laid when they were dead and gone. Instead, that morning was lovely, and cool because of the rain. It was the kind of morning that Dean liked to spend as a child sitting and reading, while occasionally glancing out the water spattered windows.

It reminded him of his childhood, and that nostalgia that suddenly came over him was tinted with sorrow.

“G’bye, Bobby.” Dean saluted the now completely filled grave. The men who had been working on filling Bobby’s grave were drinking sodas off to the side, talking and laughing. Dean sighed and stuffing his hands in his pockets, began to walk back to the Impala. He had work to do today. In lieu of Bobby’s death, Dean had closed up the Singer Salvage Yard that he was now in charge of, for the day.

Dean’s life had been a hard one. His mother, Mary Winchester, had died in a house fire in the dead of night. Dean had been five years old, and his baby brother had been barely a year old. Dean could still call to his mind an image of their house in Lawrence burning to the ground. Plumes of black smoke rose into the sky, a fiery blaze slowly licking away at their beloved house. His father, John, had never been the same after, and he died soon after, barely four months after the incident. Officially, doctors said that John had died of a stroke, but Dean knew better. Dean knew he’d stopped trying to live the moment Mary died in that damn house. He had seen it in his father’s eyes. He had seen the light in John’s eyes extinguish. Dean had tried, oh how he’d tried. He had sobbed in his father’s arms, and even as John’s arms automatically slipped around his tiny body, there was no comfort to be found. Dean had brought Sam, trying to induce some sort of will in his father, some will to bring himself back from the brink and take care of his children but it was no use.

Four months after the incident, John passed away, not from a stroke. From grief. Dean would know. He’d watched the slippery slope John skidded down. There had been no pulling him back. For years, Dean had blamed his father, but as he revved up the Impala and pulled away from the rain slicked curb, he understood. He’d had it slightly differently though.

Dean had blamed his father for a lot of things as he got tossed from one children’s home to another, but the one thing he despised him for, was for Sammy getting taken away. Young, and cute, Sam had been adopted in a heartbeat. Dean still remembered what it was like. Six years old and too young to understand that this was goodbye, he’d kissed his brother on the cheek and waved as his two year old brother was taken away from him forever. “Come visit lots!” He’d yelled as they left.

His social worker Page had given him a tube of M&Ms and congratulated him on being such a good boy. Happy with the candy, Dean had laughed and smiled, happy for his brother, and secure in the belief that he’d be able to see Sam, and play an important part in his life. Every weekend, he sat by the window facing the road of the children’s home, and waited for Sam to come visit. Dean didn’t remember much else other than those cold morning spent waiting. He didn’t remember the name of the homes he’d been in as a child and he didn’t remember the names of the other children. The only things he ever held onto were the names of his parents and the name of his little brother.

It took three years for Dean to come to the realization that Sam was never coming to visit. When he finally got it, he was less affected than he thought. That first morning that he didn’t wait by the window, his caretaker had asked him why he wasn’t waiting at the door.

His answer had been simple: “He isn’t coming.”

School had been interesting to say the least. Dean laughed humorlessly at this random memory that surfaced. Elementary and middle school were uneventful. None of the other kids had wanted to play with the “kids from the home” and Dean was just fine with that. He stuck to himself either way. High school on the other hand had been a whole different ball game.

By then he’d been transferred to Hope Boys’ Home in Missouri, and had gone to the local high school. Dean never had friends; he’d never wanted them. His life had never been easy, and while he had never disturbed anyone, he by no means had trouble holding his own in unfavourable conditions to say the least. On the first day, he’d been approached by the gang of boys that ‘ruled’ the high school.

The leader, with a funny scar on the side of his face, had approached him swinging a butterfly knife with little finesse. Dean had pulled out his own, that had previously belonged to his ex-Marine father, and had taught him how to handle it properly. That had pretty much guaranteed his safety in high school, and had cemented his initiation into the little group. The guy with the scar was Gordon. There had been a lot of speculation on where Gordon had gotten his scar. Some said he got it from a tussle with a shark. Others said he’d gotten it from a bar fight. The insane rumours had always been humorous to both of them, and Gordon told him in confidence that he had actually gotten it from his drunken father lashing out at him with a whiskey bottle shard.

That had pretty much opened Dean to a life of partying, sex and lots of booze. He didn’t remember much of high school, other than dropping out when he turned eighteen, about six months before graduation. Page had sat him down for the talk.

“Are you sure you want to drop out of high school, Dean?”

“Yes.” He had answered shortly, impatient to get out of there.

“You can stay here as long as it takes to get your high school diploma Dean.” Page had told him earnestly. “It’s all taken care of.”

“I don’t want my fucking diploma.” Dean had hissed. “I want to get out of this hellhole.”

Page had looked hurt and sad, and for a moment perhaps, Dean had felt sorry for her. She had been trying to help him, but she just didn’t understand. No one ever could.

“I see. In that case, I’ve managed to get the number for your father’s old friend. As I understand, he currently owns a salvage yard. You could contact him and ask him for a job.”

“I want to see my brother.” Dean had gritted out.

“You’ve asked that many times Dean, but I’m sorry. Sam is not eighteen yet, and for now, his parents want to keep this from-“

“Fuck them!” Dean had yelled. “I’m his fuckin’ _brother_!”

He had stormed out. And he had called Bobby.

And here he was.

Was his life really any better now? Bobby had gotten him clean, given him his father’s Impala, given him a clean, warm place to stay. Out of sheer gratitude, Dean had played by the rules and gotten clean. He was glad he never got hooked onto drugs. Perhaps he would’ve…that is if he had gotten the money to do so. There was never any money around. You didn’t get an allowance if you were a kid of the state. Only parents gave you that.

Dean pulled up in front of Bobby’s house. The place he’d called home for the past ten years. Bobby had become the closest thing he’d had to a father in the time he’d been here. He’d once asked Bobby: “Why didn’t you come find me before, Bobby?”

“I’d wanted to, son.” Bobby’s voice had sounded harsher than usual. “I didn’t know where to start or where you’d gone, then Karen died, and boy, I couldn’t.”

Dean had felt kind of like a dick then. “I know, Bobby.”

Neither had said anything more on the subject.

Sometimes Dean still thought of Sam. It hurt that he didn’t know what his baby brother looked like, and he’d turned eighteen a long time ago, Dean knew that. Sam would be twenty four now. If Sam hadn’t come searching for him now, it meant he simply did not want to get involved in Dean’s affairs. And Dean thought he could understand that. Sam was probably living a good life. Sam was probably nice, and kind, and smart and well adjusted; all the things Dean never would be. That was okay. Dean just hoped his brother was happy, and now at this point of his life, he was glad Sam had never known him personally. He wasn’t the kind of brother someone would be proud of, he knew that.

That didn’t make it hurt any less though.

Dean went straight to Bobby’s room. He’d packed his stuff up a long time ago, when Bobby first got so sick, he’d had to be taken to the hospital and couldn’t come home. Dean just stood there for a long moment, his eyes wandering over the bed which hadn’t been slept in for months, to the bookshelves filled with books on the occult and the supernatural, to the hunting rifle mounted over the bed. Dean chuckled halfheartedly. This room screamed Bobby. Dropping to his knees on the hardwood floor, for the first time in his life, Dean prayed. Not to God, but to Bobby.

His fingers clasped together in front of him, Dean cleared his throat, eyes shut tight.

“Hey there Bobby. I’m guessing you’re gonna be uh…pretty mad at me. I’m sorry man. For everything. I…I tried to be a good son Bobby. I was so damn grateful…for…for everything man.” Dean took a long shuddering breath, feeling tears prick his eyes. “I’m so sorry, Bobby. I can’t do it anymore. It’s time for me, and you know it…man…Bobby…” Dean broke then. He gave a strangled groan and covered his face with his hands, shaking with grief. After a long moment, Dean forced himself to his feet and wiped at his face ineffectually. His eyes were still flowing, and his vision blurred. Making his way to his bathroom, Dean reached for the Valium. Dean chuckled despite himself.

“Another one bites the dust.” Dean muttered, giving the bottle an experimental shake. It sounded like it was still half full. Making his way down to the kitchen, Dean grabbed the pad and pen Bobby always kept near the phones for messages, and scribbled a quick note.

‘Rufus-The Impala’s yours, and so’s the salvage yard and the house. I’m sorry. Dean.’

Dean pulled out the keys to his baby, and slammed it down next to the note. He took the bottle of vodka he’d bought last night from the kitchen cabinet, and uncapped it, taking a long swig from the bottle. It wasn’t his first drink, Bobby had never made him go completely cold turkey; he’d still had the occasional beer or two, but it was his first swig of hard liquor in close to seven years. Going down it made his eyes water and his throat burn with the sudden alcohol, but it felt good. Dean finished a quarter of the bottle before turning to the Valium.

He popped open the bottle and shook out a mouthful of pills, biting and chewing, scrunching up his nose at the bitter taste. He swallowed them down with some vodka, and did the same with another bunch of pills. By now, he was way too hammered to stand so he sunk down to the floor, smiling in a drunken haze.

He held the bottle aloft to the world. “No, not this time. I cannot celebrate a man’s discarded life, and will not try.” He quoted a half remembered poem by Juster, read when Bobby first went to the hospital.

“Goodbye, Bobby.” Dean whispered. “Or maybe I should say see you soon. But wait, suicide cases don’t go to heaven do they?”

The last thing Dean remembered before he passed out was hysterical laughter. Right before he slipped away, Dean realized the laughter was his own.

 

 


	2. The Big 5150

**Summary for the Chapter:**

> 5150-The Dean is on lockdown, repeat the DEAN is on LOCKDOWN.

**Notes for the Chapter:**

> So the saga continues. You didn't think I was going to leave it at that, didja? xD  
> Seriously though, this chapter is comparatively lighter, so yay?

Fuck the poets of the past my friends / There are no beautiful suicides / Only cold corpses with shit in their pants / And the end of gifts. -Anon

The last thing Dean expected was to wake up in a cold, uncomfortable hospital bed. His head ached like a bitch, and his mouth felt numb and cottony. His entire body felt like it was being weighed down and it took too much effort to move, so Dean didn’t bother trying. His eyes were sore, and adjusting to the light, and he began to focus on his surroundings. He was surrounded by white washed walls, with the overwhelming stink of sickness concealed with detergent and disinfectant.

‘Okay, I was not expecting this.’ Dean thought, groaning and turning his head with effort to look at the IV drip plugged into his hand.

The sound of boots hitting the squeaky tile floor, caught Dean’s attention. He sluggishly moved his head to where the noise was coming from and got a punch in the arm for his efforts.

“The hell were you thinking, kid?”

“Rufus?” Dean managed, squinting up. The figure was fuzzy, but the way it folded its arms over its chest was no doubt Rufus-like.

“You got that right.” Rufus frowned, his face gaining clarity in Dean’s vision.

“I’m…sorry…” Dean said, his throat clicking as he swallowed. Rufus’ features softened, and he brought a straw to Dean’s mouth and let him swallow greedily at the cool water held within the glass.

“You scared us, Dean.” Rufus muttered. “I don’t want your fuckin’ car, or your house or your auto-shop you hear me?”

“How long I have been out?” Dean asked, his heart sinking. He felt sore and his head was still hammering. Not to mention the fact that he was now probably on suicide watch. Fuck. If only he’d succeeded.

“About four hours.” Rufus told him. “I found you passed out…thank god I got to ya in time.”

‘I wish you hadn’t.’ Dean thought. He said aloud, “Am I on observation then?”

“Yeah, according to the doc, people don’t OD on Valium by accident. They got ya on 36 hour watch. I gotta leave for work soon, Dean. Take care of yourself.” Rufus squeezed his shoulder, and left.

Dean sighed, hoping to be alone, but he soon realized there was no chance of this happening. As soon as Rufus left, a ridiculously short, and scrawny security guard was planted in his room, who introduced himself as Garth.

“I guess you’re stuck with me for the next 30 hours huh, Garth?”

“Guess so, sir!” He grinned.

Dean smirked, despite himself. The great thing about failing to commit suicide was that at least you could find the humour in it later. A no-nonsense looking nurse walked in and shook her head, clucking as she looked over his chart.

“Well, Mr Winchester, looks like you gon’ be in here for the next 32 hours. I’m Missouri by the way.” She gave him a disapproving look. “Child, if your friend hadn’t found you, you would not have made it. Valium and vodka? Uh uh uh.” Shaking her head again, she walked out of the room, and Dean heaved a sigh.

It was going to be a long day.

Dean remained in bed for most of it, enduring questions about his health insurance, the checking of his temperature, and the usual questions from his doctor about whether he was feeling better. Dean didn’t even bother trying to mask his suicide attempt as an accident, knowing fully well that no one could possibly believe that. Instead, he chatted to Garth.

“Why’d you kill yourself anyway?” Garth asked, curiously. “I mean, if it’s okay for me to ask.”

Dean waved off his concern with the hand that didn’t have a needle in it. “Nah, it’s okay.” One thing that depression had taught Dean: Don’t take yourself too seriously, and it gets easier to cope with reality. “Truth is, I just had nothing left to live for. So I figured, why not.”

“But you don’t even know what the future holds, why would you just give it up like that?”

Dean shrugged. “I don’t need to know what the future holds.”

Garth then pulled out his stupid puppet Mr Fizzles, and this led the conversation to lighter topics.

Later, Missouri came back in. This time, she had a smile on her face. “Hi there, Mr. Winchester.”

“Call me Dean.”

“Well Dean, the hospital was lookin’ for some next o’kin we could inform, and we found your brother, Samuel Milton.”

Dean’s eyes widened. Holy fucking shit. “You found Sam?”

“Yeah, he’s on the next plane over to Lawrence. I expect you’ll be seein’ him tomorrow.” Missouri chuckled.

“I haven’t seen him in years.” Dean said faintly. But Missouri was already out of the room.

Dean had thought Sam didn’t want to see him. Did this mean his brother was actually in the dark about him the whole time? Or did he just want to see him now? Either way, he couldn’t wait to see Sam. Or maybe he could. They weren’t exactly meeting under the best of circumstances. Dean had always pictured a happier reunion for them, back when he was still hoping that Sam would find him. He’d let go of that a long time ago. Dean lay back and rubbed at his eyes. Garth was out on his lunch break, and he was glad. There was no one around to see the tears that rolled down his cheeks.

He must’ve fallen asleep sometime around the early hours of the morning, because when he woke up, the light was all in his face, and his hospital gown was sticky with sweat. His mouth tasted gross and his eyes were puffy and itchy. In short, he had never felt more disgusting and irritable. This was not by any means made better by the sudden appearance of some monstrous giant who was standing at the edge of his bed fucking _watching_ him.

“Can I help you?” Dean said to the stranger, snippily, still rubbing at his eyes.

“Uh, Dean? Dean Winchester?”

“Yeah.” Dean huffed, knowing he was rude, but not really caring.

“Erm, I guess I should introduce myself.” The guy laughed, tugging at the collar of his shirt. It was a really expensive shirt, Dean noticed. And the cologne scent lingering in the room was tasteful but not heavy. Dean narrowed his eyes. Did they send him some shrink or something?

“Look dude, I don’t want to talk to any shrink or anything, so do me a favour and just save it, and leave.” Dean grumped, looking around for Garth who had mysteriously vanished.

“I’m Sam.” The stranger blurted out.

It took a moment for Dean to process this, as he was still trying to find the button that would call his nurse. “Yeah, that’s great and all but…” Dean’s mouth dropped open and he snapped his gaze up to the gargantuan man, who was obviously uncomfortable.

“Sammy?” Dean whispered, suddenly hopeful.

“Um, yeah. Hey Dean.” Sam managed a nervous smile, and Dean felt like crying. He knew Sam probably wouldn’t remember him, and he wouldn’t come over and grin and hug Dean like he used to, but that didn’t l.

“Sam…” Dean mumbled, eyes wide as if he still really couldn’t believe it. “I haven’t seen you in so long man. You look good, real good.”

“It’s me.” Sam bit his lip, shuffling anxiously. “Yeah, it’s been a while.” A shadow of something akin to anger passed over Sam’s face but it was gone within an instant.

“I thought your parents didn’t want you to see me, Sammy.” Dean’s eyes filled up with embarrassing tears. (Don’t judge him, he’d had a tough couple of days.) “If I’d known I’d have come out to see you…you know, under better circumstances.” He gestured to his bedridden, IV-hooked self, with a wan smile.

Sam managed a weak one in return. “Yeah. Listen Dean, I’m going to go clear up some stuff with the front desk, and I’ll be clear to take you home in an hour.”

“Sounds good.” Dean said, warmly. “We can talk then.”

“Yeah, we can.” Sam stood awkwardly for another second before hurrying out.

Dean sighed. It wasn’t that he hadn’t been expecting a reunion as ridiculously stilted as this. Part of him had just wished that Sam would at least remember him. Was that so hard to ask for? Dean closed his eyes and laid his head back against his pillow. He wished even harder now that he’d just succeeded the first time he’d tried to kill himself. Because now, he knew, even if he wanted to die, he couldn’t. Not with Sam around. He didn’t know what kind of dicks would keep their foster son from his own brother, but either way, Dean intended to stick around and resurrect whatever relationship they could from the ashes of their familial ties.

It wasn’t going to be easy though, Dean knew. But since when was easy the Winchester way? Bobby would’ve told him to keep at it. The greatest comfort for Dean perhaps, in this moment, was that Bobby would’ve understood. He would’ve understood Dean’s choice of suicide when there was nothing left to live for. When all had been taken away, the only real thing a person had left was his life. That should be his own right or decision to take. But all that was done now. Dean had Sam. He didn’t want to fuck things up with his own death before they could even get a chance to get to know each other. Dean chuckled out loud, with a sort of morbid humour. The funny thing about being so sunk in depression, is that you start to joke about it. It’s a coping mechanism more than anything. And Dean really, really, _really_ needed to cope.

Four hours later, the administration work was done, Dean had said goodbye to both Missouri and Garth, with promises to visit (He was planning on fulfilling those) and strict instructions as to his diet. Sam drove this rental car, a shiny SUV to the curb of the hospital pick up point, and Dean hobbled in, with a grimace of pain.

“Seriously? You pick this ugly beast?” Dean begins as he gets himself into the car. His stomach is sore, and his throat still feels scratchy and uncomfortable. Also, his mouth tastes like a burp died in there trying to get out. All in all, Dean is not feeling so great.

Sam laughed. “I like it!”

“I got Dad’s ’67 Chevy Impala.” Dean informed him proudly. “She’s a real beauty.”

“Overcompensating are we?” Sam chuckled.

“Bitch.” Dean grumbled, surprised to hear Sam retort.

“Jerk.”

“If anyone’s overcompensating, it’s you with this disgusting machine.”

“I just got something that matched the goods.” Sam winked.

Dean laughed. “Sammy, I’m beginning to understand how we’re related.”

They shifted into a comfortable silence for the rest of the ride back to Bobby’s house. (It was still Bobby’s even though technically it belonged to Dean.) The first thing Dean did when he hopped out of the vehicle was to drag Sam around to the scrap yard and show off his baby. The first thing Sam did was look over the car, including its interior and whistle. Dean was pleased.

It wasn’t until Dean was making grilled cheese sandwiches for dinner when Sam decided to broach the subject they had avoided religiously the entire day. “So uh, Dean, wanna talk?”

“We’re talking aren’t we?” Dean evaded, running a hand through his wet hair. (He’d insisted on a hot shower before dinner which Sam had readily agreed to.)

“You know what I mean Dean.” Sam frowned. “You’re my brother…and I know we haven’t seen each other in more than twenty years, but somehow right now, I feel like we’re just picking up where we left off.”

“God, you’re such a girl.” Dean flipped the sandwich onto a plate and pushed it onto the table in front of Sam.

“Dean.” Sam gives him a face so pouty and bitchy that Dean bursts out laughing.

“Holy shit, you have a bitch-face!”

“I don’t!” Sam squealed.

“You do!” Dean grinned, pointing the spatula at him.

Sam sighed, resignedly, but he broke into a reluctant smile. “Still Dean, we really have to talk. You did try to kill yourself.”

“It’s not that big a deal.” Dean shrugged.

“Dean you could have died!”

“So what Sam? I had nothing, okay? Things were shit!”

“If you’d died, I would have only gotten to know I had a brother, _after you were fucking dead!_ So don’t give me that bullshit okay?”

Dean was stunned into silence. Sliding across from his brother with his own sandwich, Dean gestured to the other man’s plate. “Go on and eat up Sammy.”

Sam unhappily picked up his sandwich and bit into it. “It’s good.” He muttered.

Dean smiled. “When you were little, I used to be the only one who could make you eat. Mom’d get so mad, but then I’d ask you to eat, and you’d just do it.”

“Oh.” Sam blinked, then smiled back.

“I’m not going anywhere Sammy.” Dean told him, with a note of finality in his exhausted voice. “I promise.”

And Winchesters don’t break promises.

**Notes for the Chapter:**

> Leave a comment or a kudos if you liked it! Or maybe both? <3


	3. Welcome to the City!

**Summary for the Chapter:**

> Some brotherly bonding ensues...  
> There have been some plot changes, and the editing is a little wonky. My apologies! Sam's foster dad is Gabriel not Balthazar! So sorry :/

**Notes for the Chapter:**

> So this one comes a little early. Contrary to what I expected, this fic seems to be just writing itself, so we'll see how it goes!

“They see you. They see you keep going even when all the choices keep getting taken away.”  
–Rick, The Walking Dead

“Hey Dean.” Sam smiled at him, slightly charred pancakes stacked on a plate.

Dean rubbed a palm over his forehead and eyes. “Mornin’ Sammy.”

Sam made a face. “You going to keep calling me that?”

“What, Sammy?”

“It’s Sam.” Sam pursed his lips together as Dean poured a generous dollop of maple syrup onto his pancakes, and stuffed his mouth with the sugary confection.

“You’ll always be Sammy to me.” Dean spoke through his full mouth, grinning cheekily at Sam’s sheer disgust.

“Gross, Dean! Chew first!” Sam snipped, throwing a washcloth at Dean’s head. Dean just ducked.

“Sammy you throw like a girl.”

“Jerk!”

“Hey! Be nice, I’m the one who tried to kill himself.” Dean joked.

Sam’s smile immediately faded. “That’s not funny.”

“It so is.”

“Don’t joke about that.”

“That’s the only thing I can do, Sam.” Dean said, solemn this time.

Sam sighed but let it go. “So listen Dean, I was thinking…you should come home with me to New York.”

“What?” Dean had not been expecting this.

“You know how I’m a lawyer right?”

Dean’s eyes crinkled with pride. “Yep. A hotshot in NY.”

Sam blushed. “Anyway, it means I can’t take off work for long. I’m expected back by Monday.”

“But that’s only three days!”

“Yeah, exactly.”

“I understand. We could talk on the phone, and you could-“

“No, Dean.” Sam interrupted. “I want you to come live in my apartment with me and my girlfriend, Jess. It’s time my parents met you too.”

Dean’s eyes hardened. “I don’t want to meet your parents Sam.”

“Dean…”

“No. They kept you from me man.”

“I know, Dean!” Sam argued. “And I gave them shit for it! But you need to come live with me in New York for your own good!”

“I’m not going to try to kill myself again, if that’s what you’re worried about.” Dean said, hotly.

“I know man, but I want you around.” Sam turned on the puppy eyes. Dean got a sudden flashback of that same look on two year old Sammy.

“Goddammit.” Dean glared at his brother. “Fine. I’ll come to New York, but only for a few weeks at most.”

Sam nodded furiously. “Sure, sure! I’ll book you a plane ticket.”

Meanwhile, Dean called Rufus.

“Hello?”

“Hey, Rufus, it’s me, Dean.”

“Oh hey Dean. You alright, kid?”

“Yeah, listen, Sam-“

“Your brother?”

“Yeah, he’s in town. He wants to take me back to New York.”

“That’s good, a vacation might help ya.”

“Yeah, so could you handle the auto-shop for me?”

“Kid, I’ve been handling that auto-shop just fine with or without ya. You go and take care o’yerself now.”

“Right, thanks Rufus.”

He hung up almost disappointed that Rufus hadn’t made him stay.

He took Sam to their old house. By now, it was housing another family, and had been done up to its former glory. Sam stared at it without much recognition as Dean talked.

“This was our old house. The fire started in the kitchen. Apparently Dad fell asleep at the kitchen table after leaving the stove on. I don’t think he ever forgave himself for it, so he died just a few months after Mom died.”

“I don’t remember any of it.” Sam murmured.

“You wouldn’t.” Dean said. “You were only little.”

“Yeah but there’s these fragments y’know?” Sam looked over at Dean, who was leaning against the Impala. “I’m still terrified of fire. My therapist says it’s because of what happened and we’re trying to work through it. He’s really great, and he’s really helped me through a lot of my issues, especially with what happened with my parents.”

“Foster parents you mean.” Dean gritted out.

Sam gave him a look. “Anna and Gabriel raised me Dean.”

“Anna and Gabriel kept you away from me.” Dean kicked at the tar, not looking at Sam.

“My therapist said they thought it was best for me.” Sam said softly. “He said I shouldn’t be mad at them for it.”

“Yeah, well your shrink doesn’t know jackshit, okay? Maybe you’re not mad Sam, but for years, I thought you didn’t want to know me. If I had known you, man, if I had just had some family, maybe things wouldn’t be this way.” Dean told him, hot tears springing to his eyes, which he hurriedly blinked away. “28 years spent, knowing I had family but that I could never see them? That fucking sucked, Sammy.”

“I’m sorry, Dean.” Sam sighed, clapping his brother on the shoulder. “If I had known, I swear, I would’ve never left you alone.”

Dean pushed him away before the giant could hug him, with a half grin. “You’re such a girl, Sammy.”

Sam huffed and gave him a bitch-face. Dean leaned back against his beloved car and rolled his eyes heavenward. “I’m just not looking forward to meeting them.”

Sam gave him a calculating look. “You know what?”

“What?” Dean scowled.

“You should see my therapist.”

Dean jerked upwards. “No! Sammy, no therapists!”

“You need one! It’s either that, or some psychoanalyst from the hospital, Dean!”

“Yeah how bout, fuck no!” Dean folded his arms, chin jutting out. “There’s nothing I want to talk about with a fucking shrink.”

Sam’s puppy eyes work miracles.

Which is why, on Sunday, not only was Dean headed to New York on a plane and the only one in a t-shirt and jeans in business class, he also had an appointment with Sam’s almighty therapist booked for Monday.

Dean downed the complimentary champagne and asked for a beer, while Sam sorted through papers in a briefcase. He had some big medical malpractice lawsuit on Wednesday, and he was making lots of money. Dean was proud of his brother, but it also made him painfully aware of just how worlds apart they were. Dean was just a small town mechanic with troubled history, and Sam was a bigshot in the law industry, with a loving family and wealth at his disposal. Anna herself was a lawyer and Balthazar worked from home, doing some internet business that Sam hadn’t really described. Either way, Sam had had a privileged childhood, having had an Ivy League education his entire life, while Dean had dropped out of high school as soon as he was legally able to leave the orphanage at which he’d spent half his life. Sam was in a loving committed relationship with an English teacher named Jessica, whom he was so obviously smitten with. They would be married within the next four months.

Dean was way out of his league with his own brother, and the thought made him more than a little uncomfortable. Here Sam was, with a good career, home life, and now a beautiful (Sam had shown him pictures.) and smart fiancée. Things were going great for him, and Dean wasn’t sure he could fit into a life like that easily. Sam seemed to want him around, so that was good, right? Dean sighed and as the plane started to taxi, he glugged his beer, and asked for another one, screwing his eyes shut, and humming to himself.

“Uh, Dean?” Sam was giving him a strange look, and Dean dug his fingers into the armrest while giving his brother a watery smile.

“Yeah, Sam?” Dean’s voice wavered.

“You okay?”

“I’m uh…scared…of flying.”

Sam, the little bitch that he was, burst out laughing, ignoring Dean’s glare. “Dude, that’s hilarious!”

“Gee, thanks Sam, I hope you find it hilarious when we fall out of the sky in this fucking metal box!” Dean said caustically, shutting his eyes again and gulping as the plane rose into the air.

“We’ll be fine, Dean.” Sam, that asshole, just rolled his eyes, riffling through papers.

“That’s what they all say.” Dean said weakly.

“Relax.” Sam soothed. “It won’t be long till we’re touching down in JFK Airport.”

“Great.” Dean shut his eyes and took a deep breath. “Fantastic.”

There had to be turbulence There fucking _had_ to be turbulence. Sam barely noticed, so immersed in his reading he barely registered Dean’s trembling, but snickered when he looked up, at the way Dean’s face was screwed up, his fingernails digging into the seat arm.

“We’ll be fine, they said.” Dean gritted out. “We won’t crash, they said.”

Sam rolled his eyes as flamboyantly as he could.

Dean would’ve kissed the ground at the airport if Sam hadn’t grabbed his arm and rushed him off to get their baggage and meet his family. Dean was not looking forward to it in the slightest. He was supposed to be meeting the very people who had hidden his existence for more than twenty years. He couldn’t say he liked them already. When he saw the look on Sam’s face though as they reached the exit where people were waiting, Dean had to grudgingly admit they’d raised him well. He skulked behind the behemoth of his brother as Sam greeted three people with warm hugs.

Dean waited patiently as Sam turned around and pulled him forward. Gesturing to a woman with flaming red hair with barely a hint of gray in it, Sam grinned. “Dean this is my mum, Anna Milton.”

Anna stepped forward and greeted him with a tight smile. Dean could tell she didn’t like this anymore than he did, and it did nothing to strengthen his opinion of her. He nodded and shook her hand with a mere hint of a strained smile. His posture relaxed a little more when Sam introduced him to his father, a short, but sprightly man with blonde hair swept back from his forehead.

“Dean, this is Gabriel.” Gabriel Milton literally bounced forward and shook Dean’s hand enthusiastically. Dean couldn’t help but like him almost immediately.

“Good to meet you, Dean-o.” Here, Gabriel cast a shadow of a glance with some foreign emotion, at Anna. “Pity we couldn’t have met earlier.”

Dean could have sworn it held a not-quite-tiny hint of malice in it. He looked at the man’s wife, but her face was expressionless, easing up when she looked at Sam, towering over her. Dean’s heart melted slightly at the sheer love in her gaze. At least Sam had never gone without anything in his life. Well, except a brother. Dean hardened his heart again at the very thought. Finally, the last person stepped forward, and Dean let out a muffled gasp when he got an armful of sweet-smelling, soft cloud. It took a moment for him to register that it was a human being.

It was only when the person stepped back that Dean was able to see that it was a petite young lady, with big, warm eyes and curly blonde hair. Sam wrapped an arm around her and stooped to kiss the top of her head. “You must be Jess.” Dean grinned, despite himself.

She nodded, a lovely smile gracing her features. “Hi Dean! Sam’s told me so much about you!” She gushed.

“Sam’s barely met me himself.” Dean elbowed his brother. “What’s the bitch been telling you?”

Anna made a distinctly disapproving noise (which Dean conveniently did not hear) and Gabriel snickered. Jess on the other hand, pinched Sam’s side, giggling when he squealed. “Lots of things, Dean, lots of things.” She gave him a mischievous wink, and Sam gave Dean his bitch-face, rolling his eyes at his girlfriend.

Jess walked ahead with Sam’s parents and Dean slung an arm around Sam’s shoulders. “I hope you’re planning to propose Sammy. She’s a keeper, that one.”

Sam’s eyes lit up. “You think so?”

“Yeah!” Dean chuckled. “Jess is awesome.”

“I was planning to propose.” Sam said in a low voice. “I just need to pick out a ring, and I’m all set.”

Beneath the pride and happiness, something twisted in Dean’s heart. All this time, Sam had been living a life completely separate from Dean’s. To see the evidence of this was painful, but Dean was worried about if he would ever be able to blend into Sam’s life, or forever be a neatly compartmentalized portion of it: tucked away into the past.

Sam hesitated. “Maybe you could help me out?”

Dean’s breath caught. “Sure, Sammy.”

Sam nodded, looking relieved. Dean was faced with another sudden realization: Maybe Sam was trying just as hard as Dean was to be brothers again. He wasn’t alone in this.

With that newfound understanding, Dean followed his brother out into the New York City sun.

**Notes for the Chapter:**

> Leave a kudos/comment/both if you liked it! If you did, here's a hug *hugsies*


	4. The Shrink's Couch

**Summary for the Chapter:**

> Dean meets Sam's hero: his therapist.

**Notes for the Chapter:**

> So this is early :)

“Darkness cannot drive out darkness, only light can do that.” –Martin Luther King Jr.

The nights were the hardest.

The darkness crushed you and thoughts normally deep in the recesses of your mind rose to the surface to mock and taunt you. The voices in your head carried long and furious arguments with each other, but above all they poked at you and told you you’re doomed. Dean could never sleep at night. He lay in bed and listened to the suffocating silence, feeling his chest tighten and his head pound. What was it about the night that made your deepest fears and emotions and inner monsters make themselves known again? Dean had to admit though, in Lawrence it had been worse. It got pitch black at night, and it felt like the black was choking him. At least in New York, there was always a lot of light. It kind of made Dean feel a little better.

When they had reached Sam’s apartment in the Upper West Side, Dean had been expecting to occupy the couch. Instead, he’s been put up in a nice little guest room with a queen bed and bureau. The place was pretty fucking _awesome_ , with these huge floor to ceiling windows and large open spaces. It was tastefully decorated, making the most of the space, and Dean suspected that it was all Jess’ doing. There were no walls to separate the dining room, living room and kitchen, and from that large space branched two bedrooms and one bathroom. There was yet another bathroom in Sam and Jess’ bedroom. It was obvious that Sam earned rather a lot of money. None of that really made Dean feel comfortable and he would have felt out of place if not for Sam and Jess and the welcome way in which they treated him.

It didn’t help at night though. Dean groaned and got out of bed, padding over to the large windows at the side of his room and looking out. It had a pretty lovely view of the New York City skyline, and Dean could see right into Central Park. Sighing, he pressed his forehead against the cool glass. What he wouldn’t give for some Led Zeppelin then…Fade to Black would really fit his current situation. Dean loved the night, he really did. On nights like this, he used to sneak out and take the Impala for a spin. He was pretty sure Bobby had known but never said anything, so Dean never mentioned it either. When his insomnia made him toss and turn at night, he’d slip out, start up his baby, and speed through the deserted streets of Lawrence with the windows down. He’d loved the way the wind streamed through his hair. Sometimes, he’d drive all night, until he got exhausted, then he’d make for home, where he’d crawl into bed and sleep soundly for about two hours before he woke up again. Thankfully as he began to adapt to life at Bobby’s nights like that were rare. They did, of course, start up again when Bobby was hospitalized.

Sometimes he wished there was someone there. He’d never had anyone, really. It was kind of pathetic in hindsight, that he’d never actually had a girlfriend. There’d been sex, sure, there was always sex. Dean felt like he needed the sex, as some warped sense of comfort. It was the only way he could feel like he was close to someone. He had issues, he knew that. Girls were attracted to him because he gave off an aura of ‘carefree bad boy’. They left once they realized he was nowhere near that.

Under all the leather, AXE body spray and easy smiles, Dean Winchester was a neglected, lonely kid, and he hated himself for it. Dean didn’t deserve love, he knew that. So he had sought out the closest thing to it: intimacy. He had indulged in it, smothered himself in it, that and alcohol until feelings were obsolete. Until he could feel no more. He’d figured this out by the time his 24th birthday rolled around, and all physical intimacy had stopped. He’d had no friends besides Bobby and Rufus, so he spent most of his time either at home, in the garage or driving around in the Impala. It hadn’t been all that bad. Besides, once Bobby had been admitted to the hospital, dying slowly from terminal cancer of the lungs (Dean knew all those cigarettes would come back to bite his friend in the ass), Dean divided his time between the garage and a cold hospital chair.

Getting back into bed, Dean flopped onto his back and closed his eyes with a heavy sigh. His head started whirring again as it always did, running over the events of the day and his worst memories in turn.

‘It’s Monday tomorrow.’ His brain started on its inner monologue. ‘You’ve got that appointment. Shit. I wonder how bad it’s going to be. If I survive it’ll be a miracle. The guy’s probably a gazillion years old. Probably wears those glasses that magnify the eyes or some shit. I bet he’s got a wardrobe full of argyle sweaters and keeps one of those yippy little dogs that run around and shed a lot. I hope he doesn’t ask me all these stupid questions. God. I hate talking about feelings. It’s bad enough that that’s all Sam wants to talk about. It’s like he thinks I’m gonna kill myself again or something. Hmph…well I guess he has a point. Not like I’m going to now. I bet this therapist guy’s pretty expensive. Maybe he witnessed the Middle Ages…’

________________________________________________

 

“Dean!”

“Wha…Sam?”

“Hurry up! You’re going to miss your appointment!”

“What time is it?”

“7AM.” Sam shoved Dean. Hard. “Your appointment’s at 8!”

“Sam, what the fuck? You didn’t tell me it was that early!”

“I wanted to drop you off before I had to be in court so I booked an early appointment.” Dean didn’t need to open his eyes to know Sam was giving him the bitchiest bitch face in his repertoire. “Is that going to be a problem?” Sam said, snippily.

(Yes.) “No.” Dean mumbled.

A ridiculously quick breakfast and a five minute drive later, Dean was standing in front of a forbidding gray office building. “Good luck! It’s on the tenth floor!” Sam called as he drove away. Grimacing, Dean plucked at his new clothes. Sam had bought him new clothes and had forced him into a soft forest green shirt (It was freakin’ expensive; Dean had checked the price tag) tucked into new ‘weather-beaten’ Levis. Over that, he was wearing one of those annoyingly sensible jackets from some place called Aether. The only thing Dean had really liked about it was that it had this vintage motorcycle in an LED-lit crate. Other than that, it had an atmosphere of pretentious doucheyness. Dean shuddered, and pulling the collar of the jacket up, he slipped into the building. It was late March and there was a light flurry of snow outside, and the sidewalks were lined with a thin layer of frost. Pulling off his gloves, Dean stuffed them into his pocket. The interior of the building was warm and carpeted, and Dean made a beeline for the lift, past the foyer. He had to admit, Sam had been right about the clothes. He looked normal. It didn’t really show off his body or anything, but he didn’t look out-of-place either. Not that he’d ever tell that to the litte bitch’s face, but with the clothes, he fit in as a New Yorker much more easily than when he’d been in his flannel and worn jeans. Dean got into the lift, and rode it up to the tenth floor where he nearly choked at the sheer opulence of the place.

It was grand, for a fucking therapist’s office, with a large reception area and a glass door leading to a bar with seats around it. Dean could see some really pricey liquor in the cabinets. Gulping, he made his way to the receptionist, a pretty Indian woman dressed in the standard office attire. Her nameplate said, ‘Kali’.

“Um, excuse me?” Dean attempted.

Kali looked up with a frown. Dean knew from the look on her face, she knew he didn’t belong her. With an icy tone, she asked. “Is there something I can do for you?”

“My name’s Dean, I’ve got an appointment for 8AM?”

Her face cleared and she clicked a mouse, peering at the screen. “With whom is your appointment booked?”

Dean bit his lip, cursing in his mind. “Uh, I’m not really sure, my brother kinda booked this for me…”

“Your brother?” Kali gave him a cynical look, like she thought he was bullshitting.

Dean felt so out of his element, he was getting annoyed. Shouldn’t customer service people be kind and smiley and all that crap? She was just being a bitch, and Dean was fed up. “Yes.” He said, as pissy as he could manage. “Sam Milton. My brother.”

Kali did a double take. “Mr. Milton is your brother?”

“Yes.” Dean rolled his eyes.

“Excuse me sir, I didn’t know. I believe your appointment is with Dr. Castiel Novak.” She recovered smoothly, and pointed down the corridor. “Last door there.”

Dean followed her instructions and went down the corridor, knocking on the wooden door. A brass nameplate was engraved with the words ‘Dr. C. Novak, Ph.D’.

He knocked once, then opened the door into a large and comfortable office. There was a mahogany desk with a chair behind it in one end of the room, and a bookcase and chessboard set up at the other end. In the middle of the room, there was a set of three couches placed around a low table. Dean noticed a tiny bar, and a coffee-maker behind the desk. The desk itself was sort of messy, with papers and books scattered about, like a Psychology Today magazine,and a thick volume entitled A Jungian Approach to Literature. Behind said desk was a slight man with rumpled dark hair, and cerulean eyes that watched Dean intensely as he came into the room. Dean reached the middle of the room, where the couches were situated and hung about awkwardly. The smaller man stood up and came over to Dean, sticking out a hand.

“Hello, you must be Dean. It is good to meet you.”

That voice was Dean’s undoing. It was gravelly and intoxicating, like the best goddamn whiskey money could buy, and then some. His mind went blank and his palms became clammy. He heard himself saying “Hey. Yeah so you must be the great Castiel.” (Seriously?! Get it together man!) Dean cleared his throat and shook Castiel’s hand with a little more force than intended. “Good to meetcha too.”

Castiel nodded and gestured to the couch. “Please, take a seat.”

Dean sat. The most beautiful man Dean had ever laid eyes on sat on the couch opposite him. “So what brings you here today?” Castiel began, solemnly. (Did the man never smile?)

Dean shrugged. “My brother thinks I need to go for therapy.”

“Why do you think he thinks that?”

“Because I tried to kill myself.” Dean said gruffly, watching Castiel’s face carefully to gauge his reaction.

Castiel’s face did not so much as twitch. There was no change whatsoever except him cocking his head slightly to the side. “And why did you do that?”

Dean shrugged. “Because there was nothing else to do.”

“Do you really believe so?”

That started Dean off. He began by telling Castiel about the fire, how his parents died, and how life was like at the orphanage. By the time he got to his time at high school, their time slot was over.

“I hate to interrupt you, Dean.” Castiel said, sounding genuinely apologetic. “But your time is up, I’m afraid. I have another client waiting.”

Dean blinked, and inhaled deeply. He had never in his life talked so much for so long. He bit his lip. Of course Castiel had other patients. It was stupid to feel upset or jealous. It was just that he’d told this guy things he’d never told anyone, not even Sam, about his life. It seemed so intimate; surely nothing that should be brushed off so heartlessly…He stood up abruptly. “Yeah, sure, gotcha.”

“I’ll see you next week, Dean.” Castiel nodded gravely and reached out, shaking Dean’s hand once more.

Dean lightly took his hand, and let go of it almost immediately. “Yep, see ya.”

Dean got a taxi back to Sam’s apartment. He was in a daze. “What the hell just happened?” He questioned aloud in the cab.

The driver looked at him with a sarcastic expression. His reply was no less caustic. “Did you want me to guess?”

**Notes for the Chapter:**

> Do leave a kudos/comment/both if you liked it! Makes me happy :)


	5. Dinner with the Miltons

**Summary for the Chapter:**

> S&J Forever <3
> 
> Dean has to face the Miltons, and adjust to NY life. He's having quite a busy week.

**Notes for the Chapter:**

> Another chapter. This is getting progressively more interesting to write, so I hope you're enjoying it as much as I am :)

“In three words I can sum up everything I’ve learnt about life: It goes on.” – Robert Frost

Dean didn’t get to see much of either Sam or Jess during the week. Sam left rather a considerable amount of money for Dean to do whatever he wished during the day, and he made use of the free time and money to get lost as much as possible. It was therapeutic to walk out into the streets of New York and walk through so many side streets and paths that he always ended up completely and utterly lost. He discovered some amazing places to eat through this method of exploration. He came upon a fantastic pizza place one time, and a cheap, genuine Italian restaurant another time. He also found a diner down the street from Sam’s that sold amazing cheeseburgers and malt shakes, run by a lovely woman by the name of Ellen Harvelle.

It felt good to be in a foreign city where no one knew who he was and no one cared. The weather was chilly but comfortable enough to wander out far into the middle of Central Park. One morning, he took some stale bread to the lake out in Central Park and fed the ducks there. Another day he visited the Metropolitan Museum of Art, and another day he went to the Natural History Museum. It wasn’t something he would do normally, but NYC was full of new experiences for Dean. He took a full day to decipher the subway, and stared aimlessly through the windows of the shops at SoHo.

At the end of the week, Dean felt more relaxed and at peace than he’d ever been in his entire life. The feeling was almost foreign to him, something he’d only had a taste of from his routine with Bobby. Dean knew it was something he should hang on to, but at the same time he was too used to being indifferent to the world. He’d been depressed for so long, he had forgotten what it felt like to be truly happy again. Perhaps that was the worst feeling. He knew he was close to happiness but simply couldn’t hang on because it wasn’t familiar. He’d accepted his sadness a long time ago, but now he was questioning if it was the right thing to do in the first place. He was waiting for the other shoe to drop. He was waiting for the sadness to come creeping in, painting everything black as it always did.

Why would this time be any different?

‘Because _Sam_.’ He told himself, time and time again. ‘Because of Sam.’

Would Sam really be enough though?

The questions and worries raced through his head at night, keeping him awake well into the morning. He’d never had a good sleep cycle really. It had just gotten worse since Bobby’s hospitalization. Even sleeping pills didn’t work anymore, or at least they wouldn’t if Sam would let him have them. It wasn’t like it would be difficult for Dean to go out and buy over-the-counter sleeping pills himself, but he didn’t want to push at Sam’s buttons. It was weird; they were brothers, but they were so cautious around each other. Careful not to tease too much, careful not to push too hard: that was the way they functioned. They tiptoed around each other so daintily. Dean was grateful for it, he didn’t want to move too quickly.

When Saturday finally came, Dean was wary. Today was the day he was to have dinner with Sam, Jess and his family. He supposed he should be thankful that Anna and Gabriel hadn’t adopted any more children. Two Miltons to deal with were more than enough, thank you very much!

“Morning Dean!” Jess greeted with a big smile. Jess was always perky, even in the morning. Dean put it down to her being a kindergarten teacher. They were all like that.

“Morning Jess.” Dean gave her a quick kiss on the cheek, biting back a yawn.

“Hey Dean.” Sam surveyed Dean over the top of his _New York Times_. His eyebrows drew together. “Rough night?”

“Yeah.” Dean sighed, plopping himself into a stool facing the breakfast bar. “Didn’t get much sleep.”

Sam made a commiserating noise and took a sip of his coffee.

“How do you like your coffee, Dean?” Jess asked, poised to pour from the pot into a mug.

“Black, thanks Jess.” Dean cupped his hands around the piping hot mug of coffee she passed him with a grateful look.

“Funny.” Jess commented. “That’s exactly how Sam likes it. No one else in his family drinks it like that.”

Dean crooked his mouth into a slight smile. “It’s how Dad used to drink it.”

“I never realized.” Sam chuckled softly, looking down into his own mug. “Guess I remember a little.”

“He would’ve been proud of you.” Dean added. “And he would’ve loved Jess.”

They lapsed into a comfortable silence as Jess served them eggs and bacon, Dean’s favourite breakfast.

“Dean, we’re going shopping today.” Sam announced as Dean shoveled eggs into his gob.

“Why?” Dean asked, mouth still full.

Sam threw him a bitch face. “Because we need to get you some semi-formal wear. You can’t show up to the Milton in a t-shirt and jeans.”

“Why not? It’s your parents’ hotel isn’t it?”

“Yes, but they don’t need another reason to kick you out.”

Fair enough. Dean shrugged. “Fine. But we’re getting pie from that place, what’s it called?”

“The Little Pie Company?”

“Yeah, that place. Their walnut apple pie is the best fuckin thing I’ve ever tasted.”

“I like their Mississipi Mud.” Jess injected.

“Apple pie beats everything else any day.” Dean scoffed.

“No way!”

That started them all off on a discussion on the best pie. Dean won. Please, when it comes to pie, Dean knows his shit.

True to his word, Sam dragged Dean off to Armani to get him a nice thousand dollar Italian suit. Dean had to admit the thing looked real good on him, but he wasn’t really comfortable in anything that wasn’t denim. Truth be told, he felt like an alien. An alien that looked like a human and dressed like a human but really just didn’t belong. He didn’t voice this to Sam though. The kid was trying so damn hard to blend Dean into his life. Dean owed it to him to try too. He couldn’t shake the nagging thought, though, that Sam’s life as a highly paid, top shot, NY lawyer was something he could just never fit into. He was too coarse, too small-town, too vulgar for this gleaming castle. He was like a crack in the glass, nothing more.

Finally, they left, weighed down with shopping bags, and fatigued, Dean started towards the car park, but Sam pulled him deeper into the mall. They continued along the line of stores like Chanel and Burberry and finally ended up at a small, upscale jeweller’s.

Sam bit his lip and stared down at Dean with a hopeful, excited look in his doe eyes. “I was hoping you’d help me out with Jess’ ring?”

Dean’s face split into the biggest grin he could manage. “Of course, lil’ bro! What are brothers for?” He marched into the store behind Sam, and still smiling toothily, gazed at the rows of rings, earrings and pendants on beds of pearly white behind the glass.

“Good afternoon gentlemen. May I just say, congratulations! We welcome customers of any sexual orientation!” A sprightly young woman with the nametag ‘Becky’ beamed at them, leaning over the counter.

Sam gave a half-shocked laugh. “N-no! He’s my brother! He’s helping me pick out a ring for my _girl_ friend.”

“Oh! Sorry!” Becky looked almost disappointed at the clarification and slid out some rings, setting them on the counter. “We have some new arrivals here…”

Dean wandered away, looking at some rings at the far corner of the store. The rings were all big, and sparkly, but they seemed so generic to Dean. He looked down at his finger absently. His mother’s ring was getting a little tight on the ring finger of his right hand. He couldn’t slide it down all the way anymore like he used to when he was a teen. That ring had a lot of history, but the silver still held up, with a bright sheen. Dean had always kept it in good condition, and the simple band still looked the same after all these years.

Dean’s head snapped up and he grabbed Sam’s elbow and led him outside the store so he could speak to his brother in private. Sam frowned at him. “What is it, Dean?”

Dean pulled his mother’s ring off his finger and held it out to Sam. “I want you to have this to give to Jess.”

“What?” Sam’s forehead creased in bemusement.

“It was Mom’s. I want you to have it. It’d go better on Jess’ finger than mine anyway.” Dean explained.

Sam’s mouth dropped open. “Dean…” The taller of the brothers soundlessly took the ring, rolling it in his fingers. “Thank you Dean….that really means a lot.” Without warning, Sam threw his arms around Dean and squeezed Dean tight.

“Oof!” Dean wheezed and patted Sam on the back. “You’re welcome Sammy. I know it ain’t all that much, but that ring’s got history.”

“It’s awesome.” Sam grinned, holding the simple ring up to the light.

“When you gonna ask her?”

“Tonight. In front of my _entire_ family.” Sam clapped Dean on the back.

___________________________________________

 

7.30 PM found Dean sitting stiffly at a large, round table amidst well-dressed patrons of the Milton Hotel in a suit and tie. Around him the various members of the Milton Family were seated: Sam and Jess to his right, and Anna and Gabriel to his left. Gabriel had an enormous grin on his face, in sharp contrast to Anna’s taut smile. Sam was literally squirming with anticipation and Jess was radiant and warm as she always was. Dean got the feeling she knew exactly what was going on under the façade of calmness that the Milton family exhibited and he felt an overwhelming wave of gratitude wash over him when she smiled and winked at him. He shot her a wan smile and gulped as the waiters placed a thick, beige soup in front of them. He was well into his second glass of wine, but the anxiety just wasn’t letting up.

“So Dean, what is it you do?” Anna inquired.

“I’m a mechanic.” Dean answered hesitantly.

“It’s honest work.” Gabriel supplied with an easy laugh. The tone of his voice made Dean slightly uncomfortable, and he almost felt like there was a not-so-nice implication in the innocent statement.

“I’m good at it.” Dean shrugged. “I like cars. They’re systematic and uncomplicated. If you know where to look, the problem practically presents itself.”

“That’s interesting. It’s like a science.” Jess mused, nodding encouragingly.

“So Dean, any plans to open up a garage of your own in New York?” Gabriel asked.

Sam sat up a little straighter, not really looking at anything. Dean sighed. (He’d considered it briefly.) “I’ve got the garage my uncle Bobby left me back in Lawrence. I’ve never seriously thought about leaving it.”

“I see.” Anna murmured, her eyes trained on Sam. Dean’s fists clenched as he darted a glance at Sam. It was as he’d suspected. Sam had gotten used to their arrangement, and he hadn’t entertained the notion of Dean going back to his original life in Lawrence. To Dean, that same notion was getting less attractive by the day. But eventually, he knew he couldn’t stay here. Sooner or later, Sam would want him gone for good. He wasn’t a nice person to have around. He was temperamental, prone to moodiness and had baggage the size of Antarctica. Sam wouldn’t want to be saddled with him permanently.

“I plan on staying for a while longer though.” Dean said, quickly.

“You’re welcome as long as you want.” Jess told him earnestly, her small hand on his. Sam nodded fervently beside her, his arm around his girlfriend.

“You’re my family Dean, of course you can stay.” Sam added. At this, Dean noticed, Anna’s eyes softened a little, the impersonal ice melting away. She turned towards him, and he was shocked by the kindness in them.

“You should stay as long as you possibly can Dean.” She told him, turning away abruptly. If Dean’s mouth hung agape, neither of them mentioned it.

“Speaking of family….” Sam began. Dean bit his lip, eyes trained on his brother, gripping the table-top.

“Jess.” Sam took her hands in his, a loving look in his puppy-dog eyes. “We’ve been together for six years now, and I love you more than anything. I want you to really become a part of my family, and I want to start a family with you.” Here, Sam got down on one knee, slightly awkwardly given his size, and pulled a small, midnight blue box out of his pocket. “Jessica Moore, will you marry me?”

Jess didn’t squeal or scream or giggle. She looked Sam calmly in the eye with a tender smile and ran her fingers through his long-ish hair. “You’re going to have to get a trim before our wedding darling.”

Just when Dean thought he couldn’t like his new sister-in-law-to-be any more than he already did.

She kissed Sam, and when they pulled away, Sam smirked. “Is that a yes?”

“Yes, dummy!” She held her hand out and wiggled her fingers at him. “Go on!”

Sam got this goofy, enthralled smile over his big mug and snapping open the box, he slipped the plain band onto her finger. “It was my mother’s. Dean gave it to me.”

“It’s beautiful.” Jess whispered, hugging Dean close. That started off a round of hugs and kisses, with whispered congratulations and sniffles.

“It certainly is a lovely ring.” Anna remarked, with her first genuine smile of the evening, and with that, a tentative truce was established.

Dean made several observations over the night.

  1. Gabriel and Anna did not have as perfect a marriage as would seem.
  2. Jess and Sam were perfect for each other.
  3. Rich people food is great, but he would kill for a cheeseburger.
  4. Anna is nicer than she seems, and actually has killer taste in music.
  5. To say Gabriel has a sweet tooth would be an understatement.
  6. Ever single Milton has gone to Castiel for therapy, with the exception of Jess, who has never needed therapy.



Dean sort of gets stuck on that.

He kind of can’t wait for Monday.

**Notes for the Chapter:**

> Leave a kudos/comment/both if you liked it :) Makes me happy!


	6. Boy Trouble

**Summary for the Chapter:**

> Dean kind of can't take his mind of Castiel...

**Notes for the Chapter:**

> I know it's been more than a week, but I've been so busy! So sorry! I hope you enjoy the newest chapter :)

“Waste not fresh tears over old griefs.” –Euripides

On Monday, Dean was up and dressed well before it was time to leave. He sat at the breakfast island and sipped at his coffee, watching Jess make Sam’s lunch. His brother still ate homemade sandwiches up in his office during lunch hour. Jess glanced up and gave him a quick smile as she wrapped a roasted beef sandwich in Saran wrap. “Morning Dean. Seeing Castiel today?”

“Yep.” Dean nodded, placing his cup on the cool ceramic countertop.

“Is it helping?”

Dean took a moment to think about it. “I guess so. I mean it’s nice to talk about what happened you know?”

“Are you ever going to tell Sam about what it was like before? He wants to know.”

“He doesn’t need to know Jess. I know he feels pretty damn guilty already. It wasn’t his fault.”

Jess sighed, throwing an apple into Sam’s brown lunch bag and taking a sip of her tea. “I’ve told him that so many times, but he’s convinced it’s his fault. He blames Anna a little too. He thinks if she’d let him see you, you wouldn’t have tried to kill yourself.”

Dean hesitated. “He’s sorta right about that. I was just turning the clock you know? I was going to die anyway, why not then? I had no one. But I can’t do it now. Wouldn’t wanna miss that wedding of yours.” Dean chuckled.

“I don’t want you to miss any part of our lives Dean.” Jess said softly. “Including your _own_ life. You deserve happiness Dean.”

“I wish that was true Jess.”

“It is. You’ll see.” Jess told him, pretty face set in determination.

Dean hurriedly changed tack before he started bawling. “You ever meet Castiel before?”

“Yeah, once. At a dinner party at the Miltons’. He’s very nice. If not a little quiet.” Jess smiled.

“He’s great.” The side of Dean’s mouth curved up slightly. “Real intense but great.”

“I’m glad you think so, Dean.” Sam snickered, having come out of his bedroom, still adjusting his tie. “I’d say you have a huge man-crush on Dr. Castiel.”

“Bitch I do not!”

“Do so jerk!” Sam retorted.

“My, my. I feel so blessed to have such an eloquent fiancé.” Jess remarked, sardonically.

Dean smacked Sam upside the head with a laugh. “Come on, Sasquatch. I don’t wanna be late.”

Dean may or may not have very carefully picked out his outfit that morning. He was wearing a dark grey v neck with a black jacket and thin scarf wrapped around his neck. Obviously his choice worked out well because as he walked into the reception area, Kali actually smiled at him. The real triumph however, was walking into Castiel’s office. He unwound the cashmere scarf from his neck, taking his time as Castiel ran his fingers over the spine of some books in his shelf.

“Give me a moment Dean, I was just looking for a new notebook. I seem to go through them so quickly.”

Dean stuffed his scarf into his jacket pocket, waiting for Castiel to turn around. Finally the other man seemed to find what he needed and pulled out a thin book, whirling around to address Dean. Dean had already pulled off his jacket and draped it over the arm of the nearby couch. Castiel’s blue eyes widened, and his skin flushed imperceptibly, becoming just a tad less pale. His pink lips parted slightly, and his Adam’s apple bobbed as he licked his lips. Dean felt heat rise up his arms and chest as Castiel’s heavy-lidded gaze traveled up Dean’s lean body.

(Holy shit holy shit holy shit, he looks so fucking hot like that.) Dean let a distinctly predatory smile spread over his face. “Hey Castiel.” (He knew he was getting gay vibes from that guy.)

“Hello Dean.” Castiel’s voice was a couple notches deeper than usual, and it made Dean giddy to know _he_ had done that to him. It was Dean who was having that effect on Castiel, and Dean slipped his tongue out, running the pink tip along his bottom lip, before raising an eyebrow at Castiel, as a challenge.

Immediately, Castiel’s entire face shut down. His composure was back like it had never left, and Castiel nodded at Dean and gestured to the couch. “Please, take a seat.”

Disappointed beyond belief, Dean sat on the couch, more than a little sulky. (What had he been expecting anyway? It wasn’t as if Castiel was going to fuck him into the couch right then and there.)

“Where were we?” Castiel gave him a kind glance. Just like that, Dean was off like a bullet train. He told Castiel about the rest of it. Finally, they got to the best bit: his attempted suicide.

“What made you even attempt it?” Castiel asked.

“I had nothing left to live for.” Dean shrugged.

“It did not occur to you then to look for your brother?”

“And what? Tell him he had an alcoholic, depressed, messed up elder brother with a whole lot of baggage who needed his help? Sam was better off without me. He still is…better off without me I mean.”

“I do not think Sam would hold that same point of view, Dean. You are his brother.” Castiel said, gently. “You are one of the kindest, warmest souls I have ever met. Do not doubt that.”

Dean was taken aback for a moment, but then Castiel was asking more questions and left Dean no time to think. He was exhausted by the end of the session. He wasn’t used to the endless rollercoaster of constantly fluctuating emotions all hitting him at once. Castiel told him he was intentionally sabotaging his own happiness because he felt he didn’t deserve it, and was never going to be happy. He told him that that kind of self destructive behavior had to stop, and the only way to stop it was to change his attitude.

Dean sighed when the alarm clock beeped to signal the end of the hour. He got up and stretched, catching the way Castiel’s gaze lingered on the exposed skin of his abdomen. With a small grin, he pulled on his jacket and made for the exit.

“Wait, Dean.” Castiel bit his bottom lip, like he was uncertain of what he was about to ask. “I have no more appointments until after lunch. Would you by any chance be interested in some breakfast?”

“I’d love some.” Dean blurted out, with a nervous smile.

“Good, I know a good place.” Castiel returned Dean’s smile with a small one of his own: the first one Dean had seen. It was wonderful, like a ray of sunshine that lit up his whole face. Dean couldn’t help but smile even wider.

And that was how Dean ended up drooling as the gorgeous man across from him consulted his menu. Dean was well-aware he was staring. Now that he thought about it, he’d never given as much attention to the female population. He’d never found himself watching a girl from across the bar and thinking, ‘Dear god, she’s beautiful.’ Yet here he was, thinking as he looked at Dr. Castiel Novak, ‘He’s beautiful.’ Maybe he should be freaked out by that. (Maybe…) But, it didn’t bother him much. He was too busy drowning in the clear ocean that was Castiel’s set of peepers.

Castiel looked up from his menu only to find Dean staring unabashedly at him, and Dean immediately grew flustered, peering steadfastly down at his own menu, only to look up and catch the eye of the pretty waitress across the room. He instinctively gave her a flirtatious smile as she walked over to them, and her answering blush made him want to smirk. By accident, he let his gaze drift across Castiel’s face, surprised to find the openness gone, replaced by a cold and calculating stare.

“Cas?”

Castiel started. “Yes?”

“You wanna order?” Dean asked gently.

“Oh yes, of course. The eggs benedict please.” Castiel’s usually smooth voice was slightly stilted but Dean passed it off as his companion’s inherent…weirdness.

“I’ll have the breakfast waffle, with extra bacon on the side please. Oh and a black coffee, no sugar.” Dean smiled at her again, but didn’t spare her another glance.

“What did you call me?”Castiel’s voice was quiet, and his crystal eyes bore into Dean’s, with an intensity that was making Dean’s jeans uncomfortably tight around the crotch area.

Dean shifted slightly under the scrutiny, and wet his dry lips, loving the dirty way Castiel’s eyes tracked the movement. “Cas…is that okay? I mean I won’t call you that again if you don’t-“

“No, I like it.” Castiel gave him another one of his smiles.

“Great.” Dean’s lips pulled back in a big, silly grin of their own accord. “Awesome.”

They talked for a while longer till Castiel had to go back to his office.

“You want me to walk you up?” Dean asked, hands stuffed in his jacket pockets. Castiel’s pale cheeks were tinged with red from the cold, and his lips seemed fuller. In other words, Dean couldn’t take his eyes off the man.

“That’s really not necessary, Dean.” Castiel said, firmly. “Thank you, I had a nice time.”

“We should do it again.” Dean suggested eagerly.

A shadow flitted over Castiel’s face and he bit his lip. “Perhaps.” Then he turned around and walked back into the building, leaving Dean behind as snow drifted down to the pavement.

________________________________________

 

Dean tried not to think too much into it, he really did. The more he thought about what Castiel said, the more confused and desolate he got. He just kept walking, and before he knew it, he found himself in front of The Roadhouse, the diner owned by the Harvelle’s. (He’d always had a great sense of navigation.) Dean went in; he could really use some pie.

“Hey Ellen.” He called to the woman behind the counter, as he went over to take a seat at the booth by the window. He’d just eaten, but the long walk had given him an appetite, as did the delicious aroma of freshly baked pecan pie swirling around the diner.

“Hey there Dean.” Ellen nodded at him. “Rough morning?”

Dean sighed. Ellen barely knew him, but it was as if she had some kind of sixth sense. “Confusing morning more like.”

Ellen gave him a hawk eyed look as she wiped down his table. “Girl trouble?”

Dean bit the inside of his cheek to keep from smiling. “Boy trouble, actually.”

To her credit, Ellen didn’t show any signs of surprise at this. “Good, then you won’t hit on my Jo.”

Dean gave her an affronted look. “I would never!”

“ _Boy_ trouble huh?” Jo appeared out of nowhere behind him, and Dean jerked.

“Go get him some pie, Joanna Beth.” Ellen barked.

Dean gazed at her with sincere gratitude. “You are a saint, Ellen.”

Jo Harvelle did not take after her mother. She slid into the seat opposite him and pushed his plate of pie towards him. “So….what’s his name?”

Dean ignored her in favour of taking a bite of pie. His eyes rolled up into the back of his head and he groaned. “Ungh, shooo gooood….”

“You’re not going to tell me, are you?”

Dean shot her a wolfish grin, before swallowing. “Nope.”

“Why not?”

“I barely know you!”

“So? Gotta start somewhere right?” She shrugged, flipping blonde hair over her shoulder.

“Castiel.” Dean told her around his second bite of pie.

“How’d you meet him?” She asked, curiosity even more piqued.

“He’s my therapist.”

“Oh, _honey._ ” Jo looked genuinely sympathetic.

“Hey! It’s not that bad!” Dean sniffed, defensively.

“It’s pretty bad.”

Dean sighed. “Maybe.”

“Joanna Beth Harvelle!” Ellen’s voice sounded, clear as day, from the back room.

Jo rolled her eyes. Dean could tell she had a flair for the dramatic. “Catcha later Romeo. You comin’ in tomorrow?”

“Probably.”

“We’ll continue tomorrow.” Jo warned him, wagging an index finger in his face.

“I don’t doubt it.” Dean mumbled as she walked away.

He didn’t know how it had happened, but apparently in the time he’d been here he’d made two new friends. It felt pretty good. Dean didn’t know what it was like having real friends. He’d never had time for them. Even Bobby and Rufus were really more like father figures than friends. Dean never hung out with people closer to his age. It was kind of a nice change though, he had to admit.

It was getting easier to sleep at night.

 

**Notes for the Chapter:**

> Leave a kudos/comment/both if you enjoyed it!


	7. He's Your Therapist!

**Summary for the Chapter:**

> Dean decides to ask someone out.

 “He looked at me with serious eyes, but not the kind that made me wonder what I’d done wrong. The kind that made me wonder what I’d done right.”  
-Denise Jaden

Let it never be said that Dean Winchester did not go after the things he wanted. He called Kali when he got home from The Roadhouse, pacing the length of the deserted living room, TV on with the volume turned down. He’d never done anything like this in his entire life. He never had to. Guys, girls, they all just came to him, all with the understanding that the soft tenderness in the backseat of a run-down car only lasted a night. Dean didn’t want to have Castiel for only a night. He legitimately wanted to take the other man out on a date, but he really didn’t know how. Which is why he needed to find out if Castiel would be free for lunch tomorrow.

“Drs Novak and Novak, this is Kali, how may I help you?” The bored, honeyed voice came over the phone when Kali picked up. Dean could almost imagine her inspecting her nails as she spoke to him.

“Hi Kali, this is Dean…Winchester.” He flopped onto a comfortable black leather couch, fingers tapping on the armrest.

“Ah, Mr. Winchester. What can I do for you? Would you like to be passed over to Dr. Castiel?” There was a smug quality to Kali’s voice that was rather ingratiating, but gritting his teeth, Dean pressed on.

“No, no. I wanted to ask, does Castiel have any scheduled appointments around 1PM tomorrow?”

There was a pause, and Dean heard the clicking of keys on a keyboard on the other side. “Castiel has no appointments from 1PM to 3PM. Would you like to schedule another session?” Kali asked.

“No, no it’s fine, I uh, I just realized I have something I need to do.” Dean cast wildly, looking around. “Thanks Kali.” Hurriedly, he ended the call and tossed the phone onto the couch beside him, slumping in his seat.

He was actually going to do this. He was going to try and ask Castiel out on a date. Not that he’d done anything like this before. Never. Not once. If this failed, he’d freak out and change his therapist and never see Castiel again. (Oh god, never see Cas again? Maybe he’d have to leave New York! Fuck! Wait, stop, stop, he hadn’t done shit yet, let’s not get carried away…)

“Dean?” Dean paused in his relentless pacing, and turned to Sam, who had apparently just walked in, coat in one hand and briefcase in the other.

“Hey Sam.” Dean stopped short and plastered on a smile. “What’re you doing home so early?”

“You’re going to wear a groove in my carpet.” Sam joked. “What’s up with you?”

“Nothing.” Dean answered automatically, picking at his shirt.

Sam’s eyes narrowed. “Dean. What. Is. Going. On.”

“I’maskingCasout!”

“ _What?_ ”

“I’m asking Castiel out. On a date.” Dean thrust his chin out defiantly.

“Are you insane?” Sam yelped. “You’re asking Dr. Castiel out on a date?”

“Why not?” Dean stared at his feet defensively.

“He’s your therapist Dean!” Sam folded his arms. “That’s a disaster waiting to happen.”

“No it’s not.” Dean sighed. “Look, Sam, just let me ask him alright? If he says no, I’ll leave it at that.”

Sam frowned. “I don’t think there’s an outright law against it, but it is kind of against their ethics code.”

“Sammy, if he says no, that’s it okay? It’ll be fine.”

“Just be careful, Dean.” Sam’s eyes softened. “I don’t want you to get hurt again.”

“Sam, I’m not fragile.” Dean took a step closer to his brother. “I won’t break.”

“I don’t want to lose you.” Sam’s voice was level, but the naked fear in his brown eyes broke Dean’s heart.

“You won’t lose me, Sammy.” Dean got a sharp blast of nostalgia.

_The stink of fire is heavy in the smoke filled air. Dean’s eyes sting from the haze, and baby Sam is crying. His wails resonate in Dean’s ears, and he coughs, covering Sammy’s tiny body with his own, shielding him as much as possible. “It’s gonna be okay Sammy.” Dean whispers as he huddles with his brother on the wet grass._

“It’s gonna be okay, Sammy.” Dean hugged his brother. “You won’t lose me. I’m going to be here, always.”

“I’m sorry, Dean.” Sam’s enormous body seems tiny in Dean’s embrace, like the night of the fire. “I should’ve been there, I should’ve…”

“It’s okay, Sammy.” Dean soothed. “It’s not your fault.”

“I got into a fight, with Anna and Gabriel when I found out about you.” Sam sighed, once they’d settled down on the couch. “It’s the only time I’ve yelled at them.”

“I get they’re your parents Sam. I respect that.” Dean looked over at Sam. “Kid, I’ve learnt some things in my life, and one of them is to not play the blame game. Don’t blame yourself or anyone for the things that happen. They just happen, regardless of what you do or don’t do. There’s no point in wondering what might’ve happened or what should’ve happened.”

Sam looked up at him. “Wise words.”

Dean shrugged. “It’s part of being a big brother.”

Sam smiled. “Either way, I’m glad you’re around now.”

“Sam, even if I’m not around, I’ll never stop being your big brother.” Dean told him, gruffly.

“I’m not going to make you stay here, Dean.” Sam patted Dean’s arm. “I know you’ve got your own life back at Lawrence.”

Dean ruffled Sam’s hair. “They grow up so fast.” He smirked at Sam’s indignant squeal, and got up. “C’mon Sasquatch. I found this great diner across the street that sells awesome pie.”

____________________________________________

 

“Hey Ellen!” Dean called cheerily as the brothers walked through the doors of the Roadhouse. Sam patiently waited to be introduced, and Dean gestured to his brother.

“This is my brother, Sam Milton, Sam this is Ellen Harvelle, owner of the Roadhouse. She bakes one of the best pies in town.” Dean chuckled at the look of fond exasperation she gave him. He’d been coming in here almost every day in the entire month he’d been here.

“Hi there, Sam.” Elllen gave Sam a motherly glance. “Go and take a seat, the two of you, and I’ll get some pie while you look at the menus.”

“What pie is it today?” Dean asked, eagerly.

“Cinnamon Apple.” Jo replied, tying on her apron as she walked through the back door. “Good morning Dean Winchester.”

“Good morning Joanna Beth. I would tip my hat but…” Dean gestured to his hat-less cranium with a sardonic grin.

“You must be Sam!” Jo exclaimed, suddenly noticing the large human seated opposite Dean. “I’m Jo. Ellen’s my mom.”

Sam, though obviously startled, smiled and shook her outstretched hand. “Hi Jo.”

“Dean talks about you a lot. He talks about Castiel a lot too.” Jo confided in a low voice, wincing when Dean kicked her foot. “Ow! Fine, I’m going I’m going.”

“Made some friends huh?” Sam’s eyes were light with humour, and Dean had to laugh.

“Ellen and Jo are nice. We got to talking, especially since I come in pretty much every day.”

“Is NY that boring?” Sam chuckled.

“Nah, it’s just those artsy tourist places aren’t my cup of tea. I’d rather be eating pie in here. Or walking in Central Park. Reminds me of those woods behind Bobby’s scrapyard.” Dean told Sam.

“I used to feed the ducks there when I was little. Mom used to take me for really long walks, especially back when we had Tricky, our dog.”

“You had a dog?” Dean asked, pointedly ignoring the fact that Sam called Anna ‘Mom’.

“Sure did.” Sam nodded. “He was a golden retriever. He died when I was sixteen.”

“I’m sorry. We had an old cat at the orphanage. The guy in charge, ol’ Danny Shelby, he didn’t like cats much, so the other guys and I fed her and kept her in a cardboard box in the shed. When Danny found out, he didn’t take it too well.” A shadow passed over Dean’s face. “We all got a good beating that day.”

Sam’s eyebrows bunched together. “How old were you?”

“Eleven? Twelve? I don’t know. Doesn’t matter anyway. I was sent to a different home when I turned thirteen.”

Sam’s eyes widened. “How many homes have you been in?”

“A bunch. I never kept track.” Dean said, saved from having to elaborate by the arrival of the pie.

Tucking in, Dean groaned. “Goddamn this is wonderful.”

Sam chewed slowly and swallowed. “This pie is amazing.”

“Didn’t I tell you?”

“Oh, Dean?”

“Yeah?”

“I have a confession to make.”

“What is it?” Dean’s fork paused in its migration to his mouth.

“I have no idea what a ’67 Impala is.” Sam grinned sheepishly.

“But…my car…”

“Yeah I don’t know much about classic cars.”

Dean gasped. “No brother of mine…” They spent the rest of the day discussing classic cars, and went home to Jess making lasagna.

Dean, mouth watering at the aroma of oregano and basil wafting from the kitchen, pulled Jess into a hug. “I’m so glad my brother’s marrying you.” He told her, fervently.

Jess snickered. “Go and wash up, you two. Dinner’s almost ready.”

Sam kissed his fiancée and the two brothers made for their separate bathrooms. After washing up, the gathered at the dining alcove for dinner. Sam made a point of bringing Castiel up as soon as they had all sat down to dinner.

“Dean’s going to ask Dr. Castiel out.” He informed Jess, as Dean took a sip of his chilled beer.

Dean glared at him over the neck of the bottle, but nearly choked at Jess’s reply.

“About time, don’t you think?” Jess said, coolly, pouring herself some white wine.

“You knew?” Sam gaped.

“Haven’t you heard the way your brother talks about Castiel? You’d think the man was an angel.” Jess rolled her eyes.

Dean spluttered. “I’m right here! And I don’t always talk about Cas!”

“You even have a nickname for him.” Jess pointed out, waving her fork for emphasis.

“A nickname doesn’t imply anything!” Dean protested.

“But you asking him out does.” Jess paused. “Just be careful. He _is_ your therapist, you know.”

Dean huffed, but didn’t say anything in reply. From there, they moved on to more innocent topics of conversation but Dean was stuck on Castiel in his mind. Was it really that bad an idea, that both Jess and Sam were telling him to be careful? If Cas didn’t want to go out with him, he could just say so, Dean wasn’t forcing him. (Dean would have to change therapists out of sheer mortification though.) It wasn’t as though he was in love with Cas, he just wanted to get to know the man better and if possible pursue a romantic relationship. Castiel was different, a new species, and he fascinated Dean endlessly. He made Dean laugh, and talking to Cas was a real pleasure. (Plus he was fucking gorgeous.)

Dean had spent his entire life not getting what he wanted, and by then he’d become a firm believer in getting it yourself. Which was why he was going to go down to Drs. Novak and Novak tomorrow and ask Castiel Novak out on a proper date.

“Dean?” Sam stopped Dean on his way back to his room from the dining alcove.

“Yeah?”

“It’s not that big a deal, so go for it.” Sam grinned. “Don’t be nervous, I’m sure it’ll go fine.”

Dean swore, sometimes Sam could read his mind. “Thanks, Sammy. I’ll ask him tomorrow.”

____________________________________________

 

Lucky for Dean, Castiel was on his way out of the building when Dean arrived, breath misting in the cold NY air. He beamed at the other man, stuffing his hands in his jacket pockets. “Great, I thought I would get here too late.”

“Too late for what?” Castiel cocked his head to the side. “Did we schedule an appointment for today? I apologise if I have forgotten.”

“No, no!” Dean shook his head. “I came here to ask if you wanted to grab some lunch.”

Castiel sighed, looking relieved, his ordinarily pale cheeks reddening attractively in the cold. “That would be nice, Dean. I normally eat alone, this would be a nice change.”

Dean mentally punched the air in victory. “Awesome!” He said, breathily. “Know anywhere?”

“I believe there is a new restaurant open down the street. Would you like to try that?” Castiel suggested.

“Lead the way.” Dean winked.

He tried not to hyperventilate like a thirteen year old girl when Castiel gave him a small but warm smile.

 

**Notes for the Chapter:**

> Leave a kudos/comment if you liked it! xD


	8. Of First Dates and Weak Spots

**Summary for the Chapter:**

> The title says it all.

**Notes for the Chapter:**

> Hey everyone! Finally the next chapter; nothing too dramatic here. So I was thinking, I'm kind of in the need for a break from this, and I was wondering, does anyone want to write a fanfic with me? Like come up with a story and stuff? I'd love to do a collab with one of you awesome people :> maybe even more! If you're interested, contact me here: http://nugget-basket.tumblr.com/  
> Onto the story!

“Is it weird that we’re going out?” Dean asked once they had ordered and were waiting for their food.

“Of course not. Why would it be?” Castiel raised an eyebrow.

“Because you’re my therapist.” Dean stated blandly.

“The decisions I make in my personal life are completely separate, Dean. It shouldn’t be a problem.” Castiel said, matter-of-factly. So Dean moved on to other topics.

“Do you run the clinic by yourself?”

“No, it’s owned by my brother, Uriel Novak. He owns the clinic, but he only sees to our wealthier clients. I am the only therapist who works there on a daily basis.” Castiel took a sip of his water, and Dean couldn’t help but watch his Adam’s apple bob as he swallowed. “How are you and Sam doing?”

“We’re fine. It can be kinda awkward, I guess, seeing how we barely know each other, but it ain’t all that tough. I don’t think Anna likes me much though.”

Castiel considered this for a moment. “I believe the best way around this would be to talk to Anna directly, and try to understand her. You need not forgive her, but I am sure she had Sam’s interests at heart.”

Dean’s eyes narrowed. “I don’t really know about that. She makes me uncomfortable. I bet sometimes she wishes I _had_ killed myself and spared Sam all this trouble.”

Castiel’s eyebrows scrunched up. “Do you wish that?”

Dean avoided eye contact. “I don’t know.”

Castiel’s gaze increased in intensity. “You don’t think you deserve to be saved…” He observed astutely.

Dean was saved from having to answer by the arrival of their food, and he gladly pounced on the distraction, digging in as soon as it was served.

Castiel, thankfully, got the hint, and the rest of their conversation was painless.

“What made you become a therapist?” Dean asked out of genuine curiosity.

Castiel shrugged. “It is what my entire family has been doing. My brother Michael works as a therapist in a private hospital in Boston and my brother Uriel owns the clinic I work at.”

“So you and Uriel are the only two therapists there?”

“Yes, that’s all we need, really. We provide services to a select class of clients, you see.”

“So the wealthy and powerful.” Dean raised an eyebrow.

Castiel gave him a sheepish smile. “Basically.”

“I guess it’s good money.” Dean allowed.

Castiel didn’t make eye contact, just took a sip of his water and shifted uncomfortably in his seat. “You were a mechanic were you not?”

Dean understood Castiel obviously had no interest in talking about money so he played along with the change in subject. “Yep. Had a garage and everything. Got it from Bobby.”

Castiel nodded. “He was your father figure was he not?”

“Bobby was the closest thing to a dad I’ve ever had. It was hard, watching him suffer like that. Cancer is probably the worst thing to die from. It isn’t peaceful-it’s a whole lotta pain, all at once. When he died, I was relieved.” Dean confessed. “I didn’t want to watch him suffer like that anymore.” Something about Castiel made him just blurt all his secrets and thoughts, like verbal diarrhea.

Castiel nodded, like he understood. “I never knew my father. My mother and her second husband raised my brothers and I.”

“What was your step father like?”

“He was” Castiel hesitated here, casting a cryptic look at Dean. “Hard to get along with. Michael hated him, but Uriel his own, and very close to him.”

Dean bit his lip. That could have meant anything. Castiel’s step-father could have even been physically or verbally abusive. “Hard to get along with?”

“My mother married him because of how similar he was to her, and out of a fear of raising two children alone. She had Uriel shortly after their marriage.” Castiel told him. “I was raised to be very religious.”

“And are you?” Dean smirked.

Castiel gave him a shy smile. “They were overzealous and even at that age I realized that. So no, I cannot say that I became religious. I think that was why my father left my mother in the first place. I can’t say I blame him, exactly.”

“Is that why you three are all named after angels?”

“As far as I know it was my mother’s idea.” Castiel chuckled.

“You still talk to her?”

“She died a few years ago…Uriel took it particularly hard.” Castiel cocked his head. “Michael did not even attend the funeral. My step-father died a few months after she did. I think he loved all along.”

Dean ate his food without replying, painfully aware of how heavy their conversation was for a first date. Desperate to change the subject he began: “Is the weather in New York always like this?”

To that, Castiel only laughed.

________________________________________

 

“So I had a nice time.” Dean shoved his hands into his pockets awkwardly in the reception area of Drs. Novak and Novak.

Castiel nodded solemnly. “As did I Dean.”

Dean smiled shyly. “Could we maybe do this again?”

“Of course. It is nice to have lunch with someone. I usually eat alone.”

“So tomorrow? Same time?”

“I will see you then.”

“Alright…bye then!”

“Goodbye Dean.”

Dean watched Castiel walk into his office, a goofy smile on his face. It wasn’t until the door to Castiel’s office clicked shut that Dean became aware of brown eyes boring into his.

“You’ve got it bad, haven’t you?” Kali stared at him over her computer, a smug grin playing on her lips.

“What?” Dean stalled, bewildered.

“Uriel isn’t going to like this.” Kali sing-songed, returning her gaze to the lit screen casting a glow on her made-up profile.

Dean blinked. He didn’t see any point in hiding what he felt for Cas because apparently Kali was perceptive (He was beginning to think it was a girl thing) so he challenged her instead. “And why would I give a fuck about Uriel?”

Kali sighed, seeming to think it was pointless to talk to him. “Uriel runs this joint you uncultured bumpkin.”

“So?”

“Castiel doesn’t know anything, Dean.” Kali said, sympathy in her usually stony eyes. “He thinks these are the activities of a friend.”

“What do you know?” Dean hissed. “Why do you even care anyway?”

Kali rolled her eyes, not bothered by his anger. “I’m trying to give you a heads up, you ignorant idiot. I suggest you leave Castiel alone and go back to your little village.”

Dean bit his lip, more than a little conflicted by this point. To him it seemed like Kali was telling the truth but he was confused as to how Uriel came into play here. He shook his head. “I’ll be back.” He assured her, before walking out, footsteps brisk and firm on the parquet flooring.

It didn’t leave Dean though. He had always been a bit of an overthinker (okay maybe a lot) and this new snippet was giving his head grief. He wasn’t too sure why Castiel was so special. If it was anyone else, he knew he would’ve given up by now. He’d spent his entire life wallowing in the disrespect of others and the belief that he wasn’t good enough, that he deserved to be treated the way he was. See, the thing was, Dean hadn’t always been like this. Once upon a time he’d been full of hope and joy, especially when he was in Martha’s Home for Boys. But then he’d grown too old to stay and the rest of the homes would never match up to Martha Jenkin’s way of running things. She’d been the closest thing he’d ever had to a mother.

It wasn’t like there hadn’t been others. He’d messed around with a bunch of guys and girls, but nothing ever lasted. Eventually they were just looking for some way to push the pain to the back of their minds and give in to the mindless pleasure. That wasn’t exactly a good foundation to base a relationship. Castiel was too pure, too good to taint like that. He wanted more. He wanted to curl up in Cas’ arms while watching Lord of the Rings, and maybe Cas would make him hot cocoa on cold nights and maybe they’d stay in bed together on the weekends and maybe Cas would fall in love with him the way Dean surely was…

Oh. He was actually falling for Castiel Novak. This should be a problem, Dean thought. It shouldn’t be this quick; this easy. Dean analysed as he walked, unable to find a flaw, his footfalls getting quicker and quicker. Part of him wanted to turn back, go back to Lawrence and leave this place, leave the life he was building here. Leave Castiel in the past and let time turn the memories to dust. Part of him wanted to go to Castiel and tell him exactly what he wanted, take him into his arms, and kiss him silly. Dean compromised. He went back to Sam and Jess’ apartment and curled up into a ball on his bed.

______________________________________________

 

“Hello Dean.”

“Hey Cas.”

“Greek today?”

“I do not know about you but I would prefer cheeseburgers at The Roadhouse.”

“And pie afterward?”

“Cinnamon Apple.”

And that was the exact moment Dean kissed Castiel, on a frosty New York pavement, snow drifting down around them, passers-by skirting around them, chilly air swirling around their red ears and hair, on their fifth lunch date. Castiel’s lips were cold and chapped against his, dry and perfect. The moment they moved in tandem with Dean’s, he let out a sigh, pulling Castiel into him. Moments later, they parted, eyes wide, mouths wet.

“So.” Dean grinned.

Castiel gave him a smile in return. “I must say, Dean, I have been waiting for that to happen for a very long time.”

“You know what, Cas? So have I.” Dean slipped his gloved fingers into Castiel’s and they continued down the sidewalk to the Roadhouse.

__________________________________________________

 

“I can’t believe you’ve never watched Lord of the Rings.” Dean told Castiel for what must have been the millionth time as he slotted Fellowship of the Rings into Castiel’s DVD player. The other man lived in a large studio apartment rather near to Sam’s and the living room was tastefully decorated in the minimalist style that was so popular these days. Dean joined his boyfriend sprawled out on the expanse of white softness that was Cas’ couch, and Dean clicked the play button.

After their first kiss, things had moved rather quickly. One week later, Castiel had had dinner with Dean and his family (Sam and Jess) and here they were another week after that curled up watching the LOTR trilogy. They hadn’t done anything other than kissing and making out, and maybe a little frottage, but Dean hoped that would change tonight.

“You’ll have to change therapists.” Castiel mused, fingers threading a lock of Dean’s hair absently.

“Why?” Dean asked, as the opening monologue began, showing Sauron walking into the midst of a raging battle.

“It’s unethical.” Castiel’s eyes were glued to the screen as the remnants of Sauron’s chopped off finger blew away with the wind, leaving the cursed ring behind.

“Do I still need a therapist?” Dean asked doubtfully.

Here Castiel turned intense cobalt eyes on him. “You need therapy Dean. You’re still healing.”

Dean pressed a kiss into Castiel’s jaw, pulling him closer into his arms. “If you say so, Doc.”

“I was thinking of referring you to a friend of mine, Dr. Kevin Tran.” Castiel traced patterns into the back of Dean’s hand.

“Alright then.” Dean mumbled, licking at a spot behind Castiel’s ear. Castiel reacted in a completely unexpected way, releasing a surprised moan and jerking up in Dean’s arms.

“Uhm.” Castiel’s cheeks were pink, his pupils dilated, breathing shallow.

“What the hell was that?” Dean asked incredulously.

“It seems you have found my…weak spot.” Castiel muttered, eyes downcast, eyelashes casting a shadow on his cheeks.

“Oh really now?” Dean whispered, breath skittering over the exact same spot. Castiel shuddered, fingers sinking into the soft material of his couch.

Dean placed a kiss on that exact place behind his lover’s ear, letting his tongue skate over it slightly. “Dean.” Castiel murmured, melting into his arms like butter.

“I think we’re going to have a lot of fun with this.” Dean chuckled.

“You wait till I find your – _ungh_ …” Castiel bit his lip as Dean nipped at the sensitive skin.

Dean smiled, pulling away slightly. “I’m sorry, were you saying something?”

Castiel pulled away, only to straddle Dean’s hips, bracing his palms on Dean’s chest. Slowly he lowered himself to whisper sensuously into Dean’s ear. “I’m going to ride you until you _explode_.” Dean’s eyes widened and he stared at Castiel, mouth agape, who gazed down at him, a triumphant smile on his pink lips. Dean finally found his voice.

“Yes please!” 

**Notes for the Chapter:**

> http://nugget-basket.tumblr.com MY TUMBLR 
> 
> Do contact me if you're interested, or follow because I do a fic rec haha.
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> Comment/ Leave a kudos!

**Author's Note:**

> Like I said, pretty dark. Sigh. Leave a kudos or a comment, if you want me to keep going. This wasn't easy to write, but I feel like it might be going someplace. Either way, I'll get started on the next installment.


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